Dropbox’s Akhil Gupta on ‘Brutal Prioritization’

12/10/20 • 40 min

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This week’s episode is all about magic pockets, nickels, cupcakes, and brutal prioritization. It’s a conversation with Akhil Gupta, the general manager and VP of enterprise at Dropbox.

Before that, he was the VP of engineering and the head of infrastructure -- running a 500-person engineering team that helped create the technical foundation for the Dropbox we know today.

Steve and Quentin will talk with Akhil about how Dropbox scaled reliably from 2,000 users in 2008 to hundreds of millions of registered users today.

Back in 2012, when Akhil first joined the company from Google, there were 30 engineers. Dropbox had emerged as a leading cloud storage provider, but it faced a clear choice: should it build its own storage or rely on the public cloud? Enter "Magic Pocket."

And that technical challenge forced him to adopt a simple philosophy: brutal prioritization.

“My anxiety always is when you get too many people in a company, you start creating problems and you start losing focus because you have so much new energy, you are growing fast and you can say, let me solve every single problem. So I wanted to give a signal to the team saying, we need to always prioritize. And prioritization is hard, prioritization is painful. And hence the word brutal,” says Akhil.

This podcast is produced by Post Script Audio in collaboration with General Catalyst.

This week’s episode is all about magic pockets, nickels, cupcakes, and brutal prioritization. It’s a conversation with Akhil Gupta, the general manager and VP of enterprise at Dropbox.

Before that, he was the VP of engineering and the head of infrastructure -- running a 500-person engineering team that helped create the technical foundation for the Dropbox we know today.

Steve and Quentin will talk with Akhil about how Dropbox scaled reliably from 2,000 users in 2008 to hundreds of millions of registered users today.

And that technical challenge forced him to adopt a simple philosophy: brutal prioritization.

This podcast is produced by Post Script Audio in collaboration with General Catalyst.

Previous Episode

Nick Caldwell, Twitter's VP of Engineering

In this episode, we talk with Nick Caldwell, the VP of Engineering at Twitter.

Nick joined Twitter over the summer, after a long career building enterprise products. He now leads a team of 700 engineers on the consumer side. That presented him with a very different set of daily challenges.

“Enterprise versus consumer is a very different mindset and approach that I see people struggle with if they aren't comfortable with it. But enterprise, if done correctly, is more like chess. Consumer products are just gambling, as far as I can tell. It's gambling plus, it's maybe like fantasy football,” says Nick.

Nick was hired at Twitter because he’s really good at managing teams and setting product roadmaps. He got his start at Microsoft, where he worked for more than 15 years leading the data platform organization.

Quentin and Steve spoke with him about those early days working in enterprise -- and how they compare to his roles at Reddit and Twitter, which have very different cultures.

This podcast is produced by Post Script Audio in collaboration with General Catalyst.

Next Episode

GitLab’s Eric Johnson on Radical OpenCore Transparency

In this episode, we’re talking to Eric Johnson, the EVP of Engineering at GitLab.

Eric oversees a distributed team of engineers at GitLab, which is one of the world’s biggest all-remote companies. And no, it’s not covid-remote -- the company is natively remote, with 1,200 people across 67 countries.

GitLab is an open-source DevOps platform that makes software development faster and easier. It has over 100,000 customers serving millions of users. We’ll hear from Eric about the technical culture inside the company that makes the platform so valuable to developers at both enterprises and startups -- and how it’s operated remotely for nearly a decade.

GitLab’s culture is based on radical transparency. Everything is meticulously documented, shared, and publicly edited. That’s a crucial piece of bringing everyone together in a remote environment. It can also be a challenge for technical executives and managers.

So why create this kind of culture in the first place?

As Eric explains, it helps remote teams make decisions very quickly, with confidence. It’s also a core piece of the platform itself -- setting it apart from other DevOps providers.